Technically, yes, you can have multiple bluetooth headsets connected. Each will enumerate as a seperate sound card. You'll be limited by your Bluetooth protocol and CPU power - effectively, a modern laptop with a decent CPU should be able to drive at least 2 I would think.
You will have issues though if you're running an OS on the Windows side newer than XP. Vista/7/8 only allow for an audio stream to be directed to one output device. There are a few programs that work around this with varying levels of success. There is also a way to work around in 7, but one stream will be delayed vs the other: http://www.addictivetips.com/window...gh-hdmi-speakers-simultaneously-in-windows-7/
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